4-Methylmorpholine → HCID 86741435, compound

HRID 543006Notes

Reaction equation

HRID 543006 reaction equation
CN1CCOCC1.ClC(OCC(C)C)=O.[CH2:16]([O:23][C:24]1[CH:41]=[CH:40][C:39]2[C@@H:38]3[C@H:29]([C@H:30]4[C@@:34]([CH2:36][CH2:37]3)([CH3:35])[C@@H:33]([OH:42])[CH2:32][CH2:31]4)[C@H:28]([CH:43]=[CH:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][C:53](O)=[O:54])[CH2:27][C:26]=2[CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH3:56][NH:57][CH2:58][CH:59]([CH3:61])[CH3:60].C(=O)(O)[O-].[Na+]>O1CCCC1>[CH2:58]([N:57]([CH3:56])[C:53](=[O:54])[CH2:52][CH2:51][CH2:50][CH2:49][CH2:48][CH2:47][CH2:46][CH2:45][CH:44]=[CH:43][C@@H:28]1[CH2:27][C:26]2[CH:25]=[C:24]([O:23][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:41]=[CH:40][C:39]=2[C@@H:38]2[C@@H:29]1[C@H:30]1[C@@:34]([CH2:36][CH2:37]2)([CH3:35])[C@@H:33]([OH:42])[CH2:32][CH2:31]1)[CH:59]([CH3:61])[CH3:60]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 12249N-MethylisobutylamineHCID 62365Isobutyl chloroformateHCID 516892Sodium BicarbonateHCID 86741436HCID 86741436, compound

Product 1

HCID 86741435HCID 86741435, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

N-Methylmorpholine (0.028 ml.) and isobutyl chloroformate (0.038 ml.) were successively added to a stirred solution of 11-(3-benzyloxy-17β-hydroxyoestra-1,3,5(10)-trien-7α-yl)undec-10-enoic acid (0.109 g.) in tetrahydrofuran (3 ml.) which was cooled to -10° C. The mixture was stirred at -10° C. for 30 minutes, N-methylisobutylamine (0.05 ml.) was added and the mixture was stirred at laboratory temperature for 2 hours. Saturated aqueous sodium bicarbonate solution (5 ml.) was added and the mixture was extracted 3 times with methylene chloride (10 ml. each time). The combined extracts were washed with water (2 ml.), dried and evaporated to dryness, and there was thus obtained as oily residue N-isobutyl-N-methyl-11-(3-benzyloxy-17β-hydroxyoestra-1,3,5(10)-trien-7αyl)undec-10-enamide.

Workup

  1. stirringthe mixture was stirred at laboratory temperature for 2 hours
  2. extractionthe mixture was extracted 3 times with methylene chloride (10 ml
  3. washThe combined extracts were washed with water (2 ml.)
  4. customdried
  5. customevaporated to dryness, and there

Sources & evidence

ORD record
ord-bc561b1dd35145eb80764f989f5ed38b
Source dataset
uspto-grants-1987_04
Patent number
US04659516

Reaction notes

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